Live authentically. Welcome to your dream waterfront oasis! This charming home, nestled in a serene spot near historic Chestertown, offers the perfect blend of community ...

Discover your dream home perched on a tranquil hill in Chestertown, Maryland. This beautiful 3-bedroom, 2.5-bathroom residence features lush landscaping and a welcoming f...

Coming soon! Beautiful cape in the coveted Mile Tree Village with a lovely in-ground pool. Stay tuned for more information and pictures.

Nestled at the end of a serene cul-de-sac in the desirable Crestview neighborhood, this expansive 3,000-square-foot home resides on a generous 0.63-acre lot, boasting a d...

Welcome to this charming Colonial four square home, nestled on the north end of Queen Street in Chestertown's historic district, just two blocks from the river. Step insi...

Coastal waterfront condo with excellent views in prestigious Chester River Landing offering amenities including a private marina, community pool, fire pit, gas grills, an...

This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of...

Very affordable with a nice .59 acre lot. A great Re-Hab opportunity. Nicely located Rancher in Chesapeake Landing. Voluntary HOA membership allows access to Worton C...

Welcome to 116 Pine Chip Road, a beautifully renovated Cape Cod in the heart of Chestertown, MD, Queen Anne's County. This 3-bedroom, 1 1/2-bathroom home has undergone a ...

Unlock the full potential of this charming colonial. This 4-bedroom, 2.5-bath home spans over 1,800 square feet and offers an exciting opportunity for visionaries, invest...

Village at Chestertown end-unit two-story townhome with 3 bedrooms and 2.5 bathrooms. The spacious first floor is open-concept consisting of a kitchen, living, and dining...

Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquility of rural living. Nestled on nearly 3 ½ acres of pristine land (main lot is 2.3...

Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, per...

Panoramic farmland views and a peaceful rural setting invite you to enjoy all that this traditional brick home has to offer. Original oak hardwood floors add classic char...

Conveniently located between Church Hill and Chestertown this home sits on a quiet cul de sac with 1.25 acre lot backing to farm fields. Fenced rear yard is great for ...

Nice wooded 3-acre lot to build your dream home! Close to Chestertown and Rt 301 for commuters. The lot has perc and septic already exists. Some of the lot has been clea...

Coming Soon in Chester Harbor. This home is located on a quiet Cul-de-sac in a water access community of Chester Harbor on the Queen Anne's side of the Chester River. Se...

Step into your dream home just outside of Downtown Chestertown, recently updated with new flooring, fresh paint, and professional cleaning! This inviting residence offers...

Prepare to be wowed! Stunning house in Country Club Estates. Less than 2 miles from Chestertown and close to the Chester River. One floor living. Large rear and side yar...

Welcome to a hidden oasis, just steps from Downtown Chestertown! This Byford Heights home has been meticulously maintained; featuring main level living, attached oversize...

Welcome to this delightful brick rancher, offering over 1500 square feet of living space. This home features 3 spacious bedrooms and 2 full baths, perfect for accommodati...

This 3 bedroom 2.5 bathroom Cape Cod has been recently updated and is located on one of Chestertown’s most desired streets. The sunroom provides a wonderful connection wi...

Within walking distance of Washington College, medical services, parks and schools and convenient to historic downtown arts and entertainment district, this low-mainten...

KINGS COURT! This Colonial, sited on an acre of land, is move-in ready and boasts so many wonderful features! Here are just some that are sure to pique your interest! Fre...

Welcome to this beautifully updated rancher, offering a perfect blend of classic charm and modern amenities. This home boasts an oversized detached 2-car garage and an in...

Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly r...

This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with pres...

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops and a spacious apartment upstairs. The back of ...

First time to ever be offered on the market. Nestled in a picturesque neighborhood, this contemporary home is a testament to luxury and functionality. Spanning over 3,400...

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 ...

Charming house in Country Club Estates. Located on the 14th hole with views of the Chester River. 3 beds and 2.5 baths. Potential for a 4th bedroom and potential for a...

Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. The residence features 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-m...

RARE AND UNIQUE CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the highly desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home ...

Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just ...

Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a l...

Discover the epitome of luxury living in this exquisite townhome nestled within the prestigious water-oriented community of Chester River Landing. Designed with elegance ...

****PRICE REDUCED****** Seller will consider concessions to the buyer in order to make the deal work. This is a Charming 2-Bedroom Home on 1 Acre with Scenic Farm Vie...

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an ...

Enjoy picturesque water views of Worton Creek from every room. Situated on over 2.5 acres of well maintained and landscaped property with irrigation and enjoy the water ...

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. . Custom built Cape Cod offers a ...

Charming Renovated Ranch Home in Tolchester Estates Welcome to this beautifully renovated ranch home nestled in Tolchester Estates. Recently updated, this home offers a p...

Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foye...

Where Shore living begins! Welcome to 201 Princess Anne. Located on the Queen Anne's County side of the Chester River Bridge, this well maintained home is established on...

Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new constr...

Welcome home to this 3 BR 2 bath home in Kingstown Manor, situated on 1/2 acre just seconds from the Chester River. Newly refinished flooring throughout! The gorgeous, cu...

Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easi...

This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, G...

Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting...

Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath...

Sellers offering $10,000 credit toward cosmetic repairs or settlement!!!! Cute rancher in Chesapeake Landing. Nice front porch. Large living room with a woodstove with...